What the Bermuda High Teaches Every Offshore Sailor

Between Newport and Bermuda, the high pressure system that names the route sets its own terms regardless of the forecast you filed.
Lisa and Danny Greene
At the Cooper Island Nature Reserve, Lisa and Danny Greene showed me, once again, there’s no place like home. Herb McCormick

Moments after finishing the Antigua Bermuda Race aboard the Tayana 52 Moonstone, we sailed through Town Cut into St. George’s Harbour. There was a familiar figure waving from the northern shore. It was my old mate, Danny Greene, who long ago negotiated the very same channel on the 26-footer that he regularly sailed solo from New England to the island. On one trip, however, he met a local woman called Lisa, got married, had a son, Jacob, and never left. Ever since, he departs only with the greatest reluctance and exceptionally good reasons.

If you’ve ever sailed into that mid-Atlantic archipelago, which in total comprises over 180 separate isles, you certainly understand why. For countless ocean sailors, making landfall in Bermuda is a nautical rite of passage.

I’ve lost track of how many times I’ve sailed in and out of the place, but I certainly remember the first time, as a stopover on a trip from Rhode Island to the Caribbean with my pal Ricky Viggiano, the marine-electronics maven, on a Freedom 44 some four decades ago. It was my first offshore voyage, and I still remember the sense of accomplishment—as well as my inaugural Dark ’n’ Stormy—quite well. I loved those earliest nights at sea. Such a singular, wild experience. And the wonder and joy of making landfall in what is unquestionably a sailor’s paradise. In many respects, I’ve been chasing that Bermuda high ever since.

Along the way, I knocked off a couple of Newport Bermuda Races, that classic 635-nautical-miler whose success or failure is generally assured by how well one negotiates the Gulf Stream that bisects the course. After crossing the finish line, you tie up at the Royal Bermuda Yacht Club in the bustling city of Hamilton, usually greeted by a fresh tray of those Dark ’n’ Stormies. Hamilton is fine, but I’ve always preferred the relatively quiet, historic burg of St. George’s at the other end of the island. It’s more of a sailor’s town, with the customs dock, a fine anchorage and some excellent pubs. Naturally, that’s where Danny lives.

A few years back, noted offshore sailor Steve Pettengill asked me to crew on the doublehanded leg of the Bermuda One-Two short-handed race back to Newport, and we were based at St. George’s Dinghy and Sports Club, a funky and cool little spot out near the Town Cut with a full range of facilities, including a welcoming bar. Sure, I enjoyed the rather regal Royal Bermuda YC, but the Dinghy club is definitely more my speed.

Of course, one of the reasons sailors love Bermuda is the fact that you can find skillful nautical tradesmen who do excellent work. One of them is another old mate, sailmaker Steve Hollis, whose Ocean Sails loft is right on the harbor. On Moonstone, we arrived with a mysterious crack in the boom. I gave Steve a call, and five minutes later he was on deck, scratching his chin. Of course, he had a couple of stainless-steel plates in his shop that would work just fine. The repair was complete a few hours later. Try getting that done in a day in Newport.

Danny and Lisa now have a home in the middle of St. George’s, but they still own their old place on the north shore overlooking the outlying reef, and for a couple of days I had my run of it. Now I fully understood why he never wants to leave.

On my last day there, the Greenes took me on an excursion to the Cooper’s Island Nature Reserve at the southeastern tip of St. David’s Island. Formerly a U.S. military installation (which included, among other things, a NASA space-tracking station), it had restricted access for many years, but it’s now a recreational area open to the public. It’s a fantastic place for a hike, with rustic trails, dramatic cliffs and incredible views of the neighboring isles and the amazing, unmatched turquoise waters. In a way, it was the perfect bookend to an adventure that had started in Antigua, another island with vistas that are otherworldly.

The next afternoon, Danny dropped me off at the airport for my return flight to reality. Unlike my pal, sadly, I couldn’t stick around Bermuda forever.